Class targeted metabolomics: ESI ion trap screening methods for glucosinolates based on MSn fragmentation

Rochfort, Simone; Trenerry, V. Craige; Imsic, M.; Panozzo, Joe; Jones, Renee

doi:10.1016/j.phytochem.2008.02.010

Cited by 119 publications

(96 citation statements)

References 28 publications

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“…The last one is glucoerucin and was detected via its hydrolysis product 4-(methylthio) butyl isothiocyanate (erucin) (0.8%) (see Supplementary Materials). The identification of the former compounds was confirmed by the fragmentation pattern of the intact compounds that were analyzed by LC-MS, where daughter ion of sulfated glucose moiety appeared in the three compounds at m/z 259 (Rochfort et al 2008). Glucoiberverin, glucoiberin and glucoerucin were detected similarly by LC-MS in different Brassicaceae plants broccoli, cauliflower and Eruca sativa (Lelario et al 2012).…”

Section: Glucosinolates and Volatile Constituentsmentioning

confidence: 82%

“…Identification of GLS hydrolysis products and other volatile constituents of the plant as well as intact GLS was based on Wiley and Nist library databases, as well as, by comparing the mass fragmentation patterns with the published data (Kjaer et al 1963;Spencer & Daxenbichler 1980;Al-Gendy & Lockwood 2003;Adams 2007;Cataldi et al 2007;Rochfort et al 2008;Al-Gendy et al 2010;Ares et al 2014). The relative percentage, the retention time and the diagnostic mass fragments of each component were determined, as shown in Tables 1-3.…”

Section: Identification Of Gls and Other Volatile Componentsmentioning

confidence: 99%

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Glucosinolates profile, volatile constituents, antimicrobial, and cytotoxic activities of Lobularia libyca

Al-Gendy

Nematallah

Zaghloul

et al. 2016

Pharmaceutical Biology

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Context: Brassicaceae plants are associated with protection against cancers due to their glucosinolate contents. Objectives: We investigate fresh leaves, roots and ripe seeds of Lobularia libyca (Viv.) C.F.W. Meissn. (Brassicaceae) to identify their glucosinolate constituents, antimicrobial and cytotoxic activities Materials and methods: The glucosinolates were identified using GC-MS analysis of their hydrolysis products and LC-MS analysis in the case of seeds. Disc diffusion (1 mg/disc) and minimum inhibitory concentration (0-160 lg/mL) methods were used to evaluate the antimicrobial activity of seed hydrolysate. In vitro cytotoxicity against colorectal HCT-116, hepatic HUH-7, breast MCF-7 and lung A-549 cells was evaluated for seed hydrolysate (0.01-100 lg/mL) using the sulforhodamine B assay and doxorubicin as a standard Results: Three glucosinolates were identified for the first time in this plant and genus Lobularia. Glucoiberverin was the major compound accumulated in the seeds and leaves, while glucoiberin and glucoerucin were detected only in the seeds. No glucosinolates were detected in roots under the same experimental conditions. Other volatile constituents, e.g., terpenes and fatty acids were only identified in the seeds. The seed hydrolysate showed significant antimicrobial activities against Candida albicans and Pseudomonas aeruoginosa (MIC ¼ 64 and 82 lg/mL, respectively). The seed hydrolysate exhibited a marked selective cytotoxicity in vitro against colorectal, hepatic and breast cancer cell lines. The IC 50 values were 0.31, 2.25 and 37 lg/mL, respectively. Discussion and conclusion: The results indicated the antimicrobial activity of L. libyca and the selective effect of the seed hydrolysate as a cytotoxic drug that is potentially more active than doxorubicin against HCT-116. ARTICLE HISTORY

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Section: Glucosinolates and Volatile Constituentsmentioning

confidence: 82%

Section: Identification Of Gls and Other Volatile Componentsmentioning

confidence: 99%

Glucosinolates profile, volatile constituents, antimicrobial, and cytotoxic activities of Lobularia libyca

Al-Gendy

Nematallah

Zaghloul

et al. 2016

Pharmaceutical Biology

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“…Structural characterization of unknown peaks was based on MS n spectral interpretation taking into account known gas phase fragmentation behavior of particular metabolite classes, such as the flavonoids (Fabre et al, 2001;Morreel et al, 2006), the oligolignols/(neo)lignans (Morreel et al, 2010a(Morreel et al, , 2010b, and the glucosinolates (Fabre et al, 2007;Rochfort et al, 2008). A rigorous search for all profiled (neo)lignans/oligolignols was applied via CSPP networks.…”

Section: Metabolite Profilingmentioning

confidence: 99%

Small Glycosylated Lignin Oligomers Are Stored in Arabidopsis Leaf Vacuoles

et al. 2015

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Lignin is an aromatic polymer derived from the combinatorial coupling of monolignol radicals in the cell wall. Recently, various glycosylated lignin oligomers have been revealed in Arabidopsis thaliana. Given that monolignol oxidation and monolignol radical coupling are known to occur in the apoplast, and glycosylation in the cytoplasm, it raises questions about the subcellular localization of glycosylated lignin oligomer biosynthesis and their storage. By metabolite profiling of Arabidopsis leaf vacuoles, we show that the leaf vacuole stores a large number of these small glycosylated lignin oligomers. Their structural variety and the incorporation of alternative monomers, as observed in Arabidopsis mutants with altered monolignol biosynthesis, indicate that they are all formed by combinatorial radical coupling. In contrast to the common believe that combinatorial coupling is restricted to the apoplast, we hypothesized that the aglycones of these compounds are made within the cell. To investigate this, leaf protoplast cultures were cofed with 13 C 6 -labeled coniferyl alcohol and a 13 C 4 -labeled dimer of coniferyl alcohol. Metabolite profiling of the cofed protoplasts provided strong support for the occurrence of intracellular monolignol coupling. We therefore propose a metabolic pathway involving intracellular combinatorial coupling of monolignol radicals, followed by oligomer glycosylation and vacuolar import, which shares characteristics with both lignin and lignan biosynthesis.

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“…However, their accurate masses indicated the presence of an additional hydroxyl substituent. This hydroxyl group was present on the alkyl chain rather than on the glucosinolate core structure because characteristic first product ions for the latter moiety were clearly observed at m/z 259 and often also at m/z 291 and 275 (Fabre et al, 2007;Rochfort et al, 2008). In Supplemental Data Set 1, these five compounds are more specifically referred to as hydroxy-(methylsulfinyl)-alkyl glucosinolates.…”

Section: Use and Validation Of The Cspp Network To Aid In Structural mentioning

confidence: 99%

“…For example, in a hexosylated compound, fragmentation of the glycosidic bond yields a hexose neutral loss of 162 D. Other examples are the losses of 42, 44, 68, and 86 D, and 28 and 44 D in negative ionization mode that are characteristic for flavones and flavonols, respectively (Fabre et al, 2001). Additionally, compared with the collision-induced dissociation of methylthioalkyl glucosinolates, that of methylsulfinylalkyl glucosinolates is characterized by a loss of 64 D (Fabre et al, 2007;Rochfort et al, 2008). Also the different linkage types in lignin dimers can be annotated by their MS 2 neutral losses (Morreel et al, 2010).…”

Section: Inclusion Of a Ms 2 Similarity Search Into The Cspp Algorithmmentioning

confidence: 99%

Systematic Structural Characterization of Metabolites in Arabidopsis via Candidate Substrate-Product Pair Networks

et al. 2014

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Plant metabolomics is increasingly used for pathway discovery and to elucidate gene function. However, the main bottleneck is the identification of the detected compounds. This is more pronounced for secondary metabolites as many of their pathways are still underexplored. Here, an algorithm is presented in which liquid chromatography-mass spectrometry profiles are searched for pairs of peaks that have mass and retention time differences corresponding with those of substrates and products from well-known enzymatic reactions. Concatenating the latter peak pairs, called candidate substrate-product pairs (CSPP), into a network displays tentative (bio)synthetic routes. Starting from known peaks, propagating the network along these routes allows the characterization of adjacent peaks leading to their structure prediction. As a proof-of-principle, this high-throughput cheminformatics procedure was applied to the Arabidopsis thaliana leaf metabolome where it allowed the characterization of the structures of 60% of the profiled compounds. Moreover, based on searches in the Chemical Abstract Service database, the algorithm led to the characterization of 61 compounds that had never been described in plants before. The CSPP-based annotation was confirmed by independent MS n experiments. In addition to being high throughput, this method allows the annotation of low-abundance compounds that are otherwise not amenable to isolation and purification. This method will greatly advance the value of metabolomics in systems biology.

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Class targeted metabolomics: ESI ion trap screening methods for glucosinolates based on MSn fragmentation

Cited by 119 publications

References 28 publications

Glucosinolates profile, volatile constituents, antimicrobial, and cytotoxic activities of Lobularia libyca

Glucosinolates profile, volatile constituents, antimicrobial, and cytotoxic activities of Lobularia libyca

Small Glycosylated Lignin Oligomers Are Stored in Arabidopsis Leaf Vacuoles

Systematic Structural Characterization of Metabolites in Arabidopsis via Candidate Substrate-Product Pair Networks

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